Self-Assembly and Chemical Modifications of Bisphenol A on Cu(111): Interplay Between Ordering and Thermally Activated Stepwise Deprotonation

Abstract

Bisphenol A (BPA) is a chemical widely used in the synthesis pathway of polycarbonates for the production of many daily used products. Besides other adverse health effects, medical studies have shown that BPA can cause DNA hypomethylation and therefore alters the epigenetic code. In the present work, the reactivity and self-assembly of the molecule was investigated under ultra-high-vacuum conditions on a Cu(111) surface. We show that the surface-confined molecule goes through a series of thermally activated chemical transitions. Scanning tunneling microscopy investigations showed multiple distinct molecular arrangements dependent on the temperature treatment and the formation of polymer-like molecular strings for temperatures above 470 K. X-ray photoelectron spectroscopy measurements revealed the stepwise deprotonation of the hydroxy groups, which allows the molecules to interact strongly with the underlying substrate as well as their neighboring molecules and therefore drive the organization into distinct structural arrangements. On the basis of the combined experimental evidence in conjunction with density functional theory calculations, structural models for the self-assemblies after the thermal treatment were elaborated.

Benefits of Hormone Therapy Estrogens Depend on Estrogen Type: 17β-Estradiol and Conjugated Equine Estrogens Have Differential Effects on Cognitive, Anxiety-Like, and Depressive-Like Behaviors and Increase Tryptophan Hydroxylase-2 mRNA Levels in Dorsal Raphe Nucleus Subregions

“…Over the years, there have been numerous review articles underscoring the importance of these factors (Gibbs and Gabor, 2003; Brinton, 2004; Bimonte-Nelson et al, 2010; Rocca et al, 2011; Maki, 2012; Sherwin, 2012; Acosta et al, 2013; Chisholm and Juraska, 2013; Fischer et al, 2014; Luine, 2014; Koebele and Bimonte-Nelson, 2015; McCarrey and Resnick, 2015). The present study adds to the growing consensus that clarity gained from understanding the impact of these parameters is critical for providing information to offer unique and tailored treatment options for women.…”

Hydrothermal Carbonization of Argan Nut Shell: Functional Mesoporous Carbon with Excellent Performance in the Adsorption of Bisphenol A and Diuron

“…In addition, the two hydroxyl groups in the BPA molecule and the two nitrogen and oxygen atoms present in the diuron molecule may optionally cause the self-assembly of the BPA and diuron via Fig. 11 Adsorption of BPA and diuron on HTC@ANS-200 fitted by the pseudo-first-order and pseudo-second-order models hydrogen bonding, which leads to multilayer adsorption [58]. Since the adsorption mechanisms of BPA and diuron were better explained by the Langmuir model, the monolayer adsorption was concluded as the major mechanism and the multilayer adsorption is minor.…”

Control of the Intermolecular Coupling of Dibromotetracene on Cu(110) by the Sequential Activation of CBr and CH Bonds

“…Herein, we demonstrate that it is possible to circumvent this approach and to tune the connectivity of a molecular layer in a more versatile way by carefully controlling the temperature 9. 15 Furthermore, the case of dibromotetracene (DBT) molecules on a Cu(110) surface is presented as an intriguing and paradigmatic case.…”